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Synthesis 2011(9): 1383-1398  
DOI: 10.1055/s-0030-1259981
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzannulated Spiroketals Using an Oxidative Radical Cyclization

Jonathan Sperry, Yen-Cheng (William) Liu, Zoe E. Wilson, Jonathan G. Hubert, Margaret A. Brimble*
Department of Chemistry, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;
Further Information

Publication History

Received 20 January 2011
Publication Date:
04 April 2011 (online)

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Abstract

The synthesis of both mono and bisbenzannulated spiroketals using an oxidative radical cyclization approach is investigated. Although unsuccessful in uncovering a novel route toward bisbenzannulated spiroketals, the oxidative radical cyclization does facilitate a new approach to monobenzannulated spiroketals such as those found in berkelic acid and in the chaetoquadrins.

Key words

spiroketals - berkelic acid - chaetoquadrin - radical cyclization - cross-metathesis

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17

Full details regarding the synthesis of compound 20 will be reported elsewhere.